KR100656149B1 - Diglyceride fat composition comprising cla ester of phytosterol and process for preparing the same - Google Patents

Abstract

A method of manufacturing high-purity diglyceride oil or fat composition by bonding conjugated linoleic acid ester of phytosterol or phytostanol to diglyceride is provided. The method provides compounds with effects for weight control, treatment of hypercholesterolemia and prevention of cardiovascular disease as well as functionality of conjugated linoleic acid and phytosterol. The titled high-purity diglyceride oil or fat composition is prepared by the steps of mixing monoglyceride; conjugated linoleic acid; phytosterol or phytostanol; and oil or fat, fatty acid or its mixture, agitating at 10 to 200rpm and reacting at 200 to 250deg.C under reduced pressure of 0.001 to 0.5torr for 1 to 10hr. In the process, the mole ratio of monoglyceride and oil or fat, fatty acid or its mixture is 1:2 to 1:80. The composition contains 40 to 99.9% by weight of diglyceride and monoglyceride, triglyceride or its mixture residue in which conjugated linoleic acid ester of phytosterol or phytostanol is bonded to 1,3-position of diglyceride.

Description

High purity diglyceride fat and oil composition combined with conjugated linoleic acid ester of phytosterol or phytostanol and its preparation method

The present invention relates to a high-purity diglyceride fat or oil composition to which conjugated linoleic acid ester of phytosterol or phytostanol is bound, and more particularly, to a conjugated linoleic acid ester of phytosterol or phytostanol to diglyceride. The present invention relates to a diglyceride fat and oil composition, a method for preparing the same, and a method for preparing the same, which are used to impart the functionality of linoleic acid and phytosterol, and to be used for the prevention of cardiovascular diseases as well as for weight control and treatment of hypercholesterolemia.

Cholesterol is a component of biological membranes and is used as a starting material for hormonal synthesis, and it is known to cause cardiovascular diseases such as hyperlipidemia, arteriosclerosis, arrhythmia, and myocardial infarction by being accumulated in blood vessels when consumed excessively. Cholesterol derived from endogenous and exogenous migrates into the small intestine and absorbs approximately 50%. In particular, the excessive consumption of cholesterol is increasing due to the eating habits of the modern society, and thus related diseases are emerging as social problems.

Phytosterol, a phytosterol known to lower blood cholesterol in the body, is absorbed by the intestinal wall and competes with low density lipoprotein (LDL) -cholesterol, which is harmful to humans due to its structural similarity to cholesterol. The mechanism of action that inhibits cholesterol absorption metabolism in the human body has already been revealed, and has been approved by the FDA as a food additive.

Phytosterol is a generic name for alcohol compounds having a steroid structure in higher plants, and may be classified into stigmasterol, spinasterol, campesterol, and cytosterol, and, for example, α in the cytosterol. -, β- and γ- types exist. Cholesterol-lowering effect of β-sitosterol (24-ethyl-5α-cholestene-3β-ol), which is the most representative substance among various phytosterol compounds, was confirmed in an experiment in male rats and human bodies (Sugano, M et al., J. Nutr., 107: 2011-2019, 1977). In addition, β-sitosterol ester compounds in which β-sitosterol is substituted with fatty acids show almost the same effect (Mattson, F. H. et al., J. Nutr. 107: 1139-1146, 1977). For example, when adult males were given 2 g of β-sitosteryl oleate daily for 5 days, blood cholesterol levels were 33% lower (Mattson, FH et al., Am. J. Clin. Nutr., 35: 697-700, 1982).

Meanwhile, conjugated linoleic acid (C ₁₈ H ₃₂ O ₂ , hereinafter referred to as 'CLA') is an conjugated isomer of linoleic acid, an essential fatty acid (hereinafter referred to as 'LA'), which is the milk of ruminants. It is a natural fatty acid found in trace amounts in muscles. For example, linoleic or linolenic acid (C ₁₈ H ₃₀ O ₂ ), a major component of vegetable oil, and the anaerobic bacterium Butyrivibrio fibroisolvens in the rumen stomach of ruminant animals such as cattle and goats CLA is produced by the hydrogenation product of In addition, conjugated linoleic acid has been reported to be produced due to the uptake of linoleic acid's carbon center free-mediated oxidation or diet in the human body. CLA means a generic name for the positional and geometric isomers of linoleic acid with conjugated double bonds in the cis or trans configuration. Cis-9, trans-11 octadecadienoic acid and trans-10, cis-12 octadecadienoic acid, which exhibit functionality, are referred to as CLA. In addition, CLA is associated with decreased incidence of atherosclerosis (Artery. 1997. 22: 266-277), improved immune function (J. Nut. 1999. 129: 32-38), and anti-cholesterolic activity (Nicolosi et al, Circulation 88 (suppl). .): 2458,1993.), Anticancer activity (Anticancer research. 1997. 17: 969-973), growth promotion (J. Nut. 2000. 130: 2981-2989), and excellent treatment effects for diseases such as diabetes. It is also known to inhibit obesity through body fat reduction (Am. J. Physiol. 1998. 275: R667-R672). Due to these characteristics, CLA can be usefully used as an active ingredient in functional foods and pharmaceuticals. In contrast, unconjugated linoleic acid has been shown to exhibit adverse effects, such as the stimulating effect on breast cancer.

The amount of CLA obtained from food has decreased significantly over the last decade. According to food content analysis, in the 1970's it was calculated that ordinary foods contain about 0.45 g of CLA per day. As milk and dairy use decreases, the current daily average CLA intake is 0.25 g. Studies show that doubling CLA intake reduces the risk of cancer, for example, so increasing CLA intake is very important for the health of the general public.

The present inventors pay attention to the effects of anti-cholesterol, reduced body fat, anticancer, immune enhancement, or diabetes prevention and treatment of conjugated linoleic acid, and lowering cholesterol, a major causative factor of various adult diseases of phytosterol, such phytosterol and conjugated linoleic acid As a result of intensive efforts to develop an ester compound of, a simple and economical manufacturing method was developed, and the phytosterol derivatives, like phytosterol, showed a cholesterol lowering effect, a weight gain inhibitory effect, and were soluble in liquid oil. Or a phytosterol derivative in which conjugated linoleic acid is ester-bonded to phytostanol.

On the other hand, diglyceride is a fat or oil composition in which a fatty acid is bound to glycerin in the first, second, or first and third positions by a transesterification reaction between fatty acids and glycerin, and is treated separately from general oils and fats called 'triglycerides'. It is becoming. Recently, diglyceride has the same process of digestion and absorption as compared to normal neutral oil, but since it is hardly resynthesized into triglyceride, it does not increase the content of triglyceride in blood and does not accumulate body fat. As it turns out, research on this is ongoing.

However, even with the advantages of phytosterols and conjugated linoleic acid discussed above, no attempt was made to apply their functionality to diglycerides. Therefore, the conjugated linoleic acid ester of phytosterol or phytostanol, which has an effect of lowering cholesterol and inhibiting weight gain, is bound to diglycerides and supplied to the body, thereby obtaining more cholesterol-lowering effects than conventional diglycerides, while lowering cholesterol. There is a need for establishing a diglyceride fat or oil composition and a method for producing the same.

In order to solve the above problems, it is an object of the present invention to provide a diglyceride fat and oil composition that can prevent not only the treatment of hypercholesterolemia but also prevent cardiovascular diseases, and obtain the functionality of reducing body fat.

It is another object of the present invention to provide a method for producing a diglyceride fat and oil composition that can impart functionality of preventing body cardiovascular disease, as well as preventing hypercholesterolemia, as well as preventing cardiovascular diseases, and having a simple and high productivity. .

In order to achieve the above object, the present invention (a) 40 to 99.9% by weight of diglycerides; And (b) a monoglyceride, a triglyceride, or a mixture thereof, the high purity diglyceride fat or oil composition comprising conjugated linoleic acid esters of phytosterol or phytostanol at positions 1 and 3 of the diglyceride. do.

In addition, the present invention is a) monoglyceride; Conjugated linoleic acid; Phytosterol or phytostanol; And mixing the fats and oils, fatty acids or mixtures thereof and stirring at 10 to 200 rpm; And b) exchanging the stirred mixture of step a) at 200 to 250 ° C. under a reduced pressure of 0.001 to 0.5 torr for 1 to 10 hours.

In addition, the present invention comprises the steps of a) mixing a monoglyceride, phytosterol or phytostanol, conjugated linoleic acid and lipase and stirring at 10 to 200 rpm; And b) exchanging the stirred mixture of step a) at a stirring speed of 10 to 200 rpm, at a temperature of 30 to 60 ° C., at a pressure of 0.001 to 0.5 torr for 1 to 10 hours. It provides a method of manufacturing.

Hereinafter, the present invention will be described in detail.

The present inventors pay attention to the anticancer properties of conjugated linoleic acid, reduction of human body fat, immune enhancement, prevention and treatment of diabetes mellitus, and lowering cholesterol, a major causative factor of various adult diseases of phytosterol. If it was supplied to the body in the form of diglycerides, it would be more effective to inhibit the accumulation of fat in the body than the existing diglycerides, and as a result of eager efforts to develop it, a simple and economical manufacturing method was developed. As with the phytosterol derivatives invented by the inventors, it was confirmed that the cholesterol lowering effect and the body fat increase inhibiting effect were completed, and based on this, the present invention was completed.

Diglyceride fat and oil composition of the present invention is characterized in that conjugated linoleic acid (conjugated linoleic acid) ester of phytosterol or phytostanol at the 1, 3 position of the diglyceride.

The diglyceride fat and oil composition of the present invention is a di- ureate that burns without accumulating phytosterols having the effect of anti-cancer, reducing body fat, immune enhancement, anti-cholesterol and diabetes prevention, and treatment of conjugated linoleic acid and cholesterol absorption. Combined with glycerides.

Conjugated linoleic acid can be prepared chemically or enzymatically by isomerizing non-conjugated linoleic acid, anticancer, anti-cholesterol, reduced body fat, immune enhancement, which are not found in unconjugated linoleic acid. Or has a strong effect of preventing and treating diabetes. In the present invention, the conjugated linoleic acid is cis-9, trans-11 CLA; trans-10 cis-12 CLA; cis-7, trans-9 CLA; trans-7, trans-9 CLA; cis-8, trans-10 CLA; trans-8, trans-10 CLA; trans-9, trans-11 CLA; trans-10, trans-12 CLA; cis-11, trans-13 CLA; And trans-11, trans-13 CLA, and more preferably cis-9, trans-11 CLA or trans-10 cis-12 CLA.

The phytosterol is preferably one selected from the group consisting of stigmasterol, spinasterol, camphorsterol, beta-sitosterol, brassicasterol, and mixtures thereof, and the phytostanol is a hydrogen substituted form of phytosterol, Preference is given to one selected from the group consisting of knol, campestanol, cytostolol and mixtures thereof.

As can be seen in the experimental example described later, the high-purity diglyceride fat and oil composition of the present invention, as a result of animal experiments have been confirmed to reduce the blood cholesterol level by reducing the absorption of harmful LDL-cholesterol, weight gain inhibitory effect, body fat increase Inhibitory effect was also confirmed. Therefore, the diglyceride fat and oil composition according to the present invention can be used as a food additive that can be used in diet, treatment of hypercholesterolemia, prevention and treatment of cardiovascular diseases. In addition, it can be widely used as a cosmetic emulsifier, a pharmaceutical emulsifier.

The present inventors invented the method for producing the diglyceride fat and oil composition of the present invention described above in two main ways.

The first method involves mixing and stirring monoglycerides, phytosterols or phytostanols, conjugated linoleic acid and fats and oils, fatty acids or mixtures thereof, and then exchanging the stirred mixtures.

a) Monoglycerides , Phytosterol  or Phytostanol , Airspace Linoleic acid , Stirring, mixing and stirring of fatty acids or mixtures thereof

More specifically, the reaction conditions are first stirring monoglycerides, phytosterols or phytostanols, conjugated linoleic acid, and fats and oils, fatty acids or mixtures thereof. In this stirring step, it is preferable to add 1 to 80 parts by weight of conjugated linoleic acid, 1 to 80 parts by weight of phytosterol or phytostanol, 1 to 80 parts by weight of fats and oils, or a mixture thereof based on 100 parts by weight of monoglyceride.

In addition, the molar ratio of the monoglycerides and fats and oils, fatty acids or mixtures thereof is preferably 1: 2 to 1:80.

In the reaction conditions, it is preferable to stir the mixed monoglycerides, phytosterol or phytostanol, conjugated linoleic acid and fats and oils, fatty acids or mixtures thereof at 10 to 200 rpm, and if the stirring speed is less than 10 rpm, the stirring power is weak and the reaction rate is low. There is a problem that is slow, there is a problem that the product color is poor when the speed exceeds 200 rpm is not preferable.

In the present invention, the conjugated linoleic acid is cis-9, trans-11 CLA; trans-10 cis-12 CLA; cis-7, trans-9 CLA; trans-7, trans-9 CLA; cis-8, trans-10 CLA; trans-8, trans-10 CLA; trans-9, trans-11 CLA; trans-10, trans-12 CLA; cis-11, trans-13 CLA; And trans-11, trans-13 CLA, and more preferably cis-9, trans-11 CLA or trans-10 cis-12 CLA.

The phytosterol is preferably one selected from the group consisting of stigmasterol, spinasterol, camphorsterol, beta-sitosterol, brassicasterol, and mixtures thereof, and the phytostanol is a hydrogen substituted form of phytosterol, Preference is given to one selected from the group consisting of knol, campestanol, cytostolol and mixtures thereof.

b) exchange reaction step of the stirred mixture

In addition, the exchange reaction of the stirred mixture is preferably carried out for 200 to 250 ° C, 0.001 to 0.5 torr for 1 to 10 hours under reduced pressure. The exchange reaction temperature is more preferably 200 to 230 ° C. If the exchange reaction temperature is less than 200˚C, there is a problem that the reaction rate is slow, if it exceeds 250˚C there is a problem that the reaction rate is too fast to control the content is not preferable, and if the reduced pressure is less than 0.001torr monoglycerol There is a problem in that the dihydride and the diglyceride is distilled together, there is a problem that the diglyceride distillation is difficult if it exceeds 0.5torr, and if the reaction time is less than 1 hour, there is a problem that the conversion rate of the material is lowered If more than 10 hours, there is a problem that the reaction is excessively progressed.

The fats and oils are preferably selected from the group consisting of soybean oil, rapeseed oil, cottonseed oil, jade oil, olive oil, palm oil, palm kernel oil, palm oil, safflower oil, and mixtures thereof, and as fatty acids, saturated or unsaturated fatty acids having 2 to 24 carbon atoms, oleic acid , Soybean fatty acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, linolenic acid, Docosahexaenoic acid (DHA) and mixtures thereof are preferred, and may be used alone or in combination of two or more thereof. It is possible, and the kind is not particularly limited.

The second method is a method of mixing and stirring monoglyceride, phytosterol or phytostanol, conjugated linoleic acid, and lipase, and then exchanging the stirred mixture.

The second method is described in detail as follows.

a) mixing and stirring monoglycerides, phytosterols or phytostanols, conjugated linoleic acid, lipases

This step involves mixing and stirring monoglycerides, phytosterols or phytostanols, conjugated linoleic acid, and lipases.

The phytosterol is preferably one selected from the group consisting of stigmasterol, spinasterol, camphorsterol, beta-sitosterol, brassicasterol, and mixtures thereof, and the phytostanol is a hydrogen substituted form of phytosterol, Preference is given to one selected from the group consisting of knol, campestanol, cytostolol and mixtures thereof.

The conjugated linoleic acid may be prepared by isomerizing a monoglyceride containing 1 to 80% by weight of linoleic acid.

The conjugated linoleic acid is preferably included 1 to 80 parts by weight based on 100 parts by weight of monoglycerides. If the content is less than 1 part by weight, there is a problem that the functionality is lowered. If the content exceeds 80 parts by weight, there is a problem that the economic efficiency is lowered.

The phytosterol or phytostanol is preferably included in 1 to 80 parts by weight based on 100 parts by weight of monoglycerides. If the content is less than 1 part by weight, there is a problem that the functionality is lowered. If the content exceeds 80 parts by weight, there is a problem that the economic efficiency is lowered.

The lipase is not particularly limited, but the use of lipozymes, 1,3-position specific lipases, non-position specific lipases, lycopus having 1,3-position specificity, or geotriose having unsaturated fatty acid specificity is used. Preferably, more preferably 1,3-position specific or non-position specific lipase is used.

The lipase is preferably included 1 to 50 parts by weight based on 100 parts by weight of monoglycerides. If the content is less than 1 part by weight, the reaction conversion rate is significantly lowered, and if it exceeds 50 parts by weight, there is a problem that the economic efficiency is lowered.

After uniformly mixing the above monoglyceride, phytosterol or phytostanol, conjugated linoleic acid, and lipase, it is preferable to stir at 10 to 200 rpm, especially at 150 rpm.

b) exchange reaction step

This step is a step of exchanging the stirred mixture of step a) at a stirring speed of 10 to 200 rpm and a temperature of 30 to 60 ° C for 1 to 10 hours.

The exchange reaction is preferably carried out at a stirring speed of 10 to 200 rpm, in particular 150 rpm, it is preferably carried out at a temperature of 30 to 60 ° C, in particular 50 ° C. If the stirring speed is less than 10rpm there is a problem that the reaction speed is slow due to the weak agitation force, if the reaction speed is faster than 200rpm, it is difficult to control the reaction. In addition, if the reaction temperature is less than 30 ° C there is a problem that the reaction is slow, if it exceeds 60 ° C the reaction is fast but there is a problem that the enzyme and the like may be affected by heat. In addition, when the reaction time is less than 1 hour, the reaction time is short and the conversion rate is not good.

After carrying out the fat composition according to the two methods described above to remove free fatty acids, free phytosterol, monoglycerides, etc. in the fat composition through molecular distillation, thereby maintaining a high-purity diglyceride containing a high content of diglycerides A composition can be obtained.

As described above, the manufacturing method according to the present invention can obtain a diglyceride fat and oil composition having a simple manufacturing process and excellent productivity, as well as anti-cholesterol, body body fat reduction effect.

Hereinafter, the present invention will be described in more detail with reference to Examples.

These examples are only to specifically describe the present invention, it will be apparent to those skilled in the art that the scope of the present invention is not limited by these examples.

(Example)

(Example 1)

1280 g of monoglyceride, 20 g of conjugated linoleic acid, 20 g of beta-sitosterol, and 5 g of lipase were mixed in a 3 l round flask equipped with a stirrer, and then stirred and stirred at a stirring speed of 150 rpm, and then stirred at a stirring speed of 150 rpm at 60 ° C. for 10 hours. The reaction was followed by molecular distillation until both monoglyceride and triglyceride were distilled off.

(Example 2)

A monoglyceride 1200g, a conjugated linoleic acid 40g, a stigmasterol 40g and a lipase 5g were mixed in a 3 l round flask equipped with a stirrer, stirred at a stirring speed of 150 rpm, solidified, and reacted at a stirring speed of 150 rpm at 60 ° C. for 10 hours. After distillation, molecular distillation was carried out until both monoglyceride and triglyceride were distilled off.

(Example 3)

100 g of monoglyceride, 80 g of conjugated linoleic acid, 80 g of camphorsterol, and 5 g of lipase were mixed in a 3 l round flask equipped with a stirrer, and then stirred and stirred at a stirring speed of 150 rpm, followed by reaction at a stirring speed of 150 rpm at 60 ° C. for 2 hours. After distillation, molecular distillation was carried out until both monoglyceride and triglyceride were distilled off.

(Example 4)

30 g of monoglycerides, 3 g of soybean fatty acid, 2 g of oleic acid, 35 g of conjugated linoleic acid, and 35 g of beta-sitosterol were placed in a 3 L flask and stirred slowly for 1 hour when reaching 250 ° C. under reduced pressure. A diglyceride fat or oil composition was prepared through distillation by distillation.

The content of monoglyceride, diglyceride, triglyceride, free conjugated linoleic acid and free phytosterol of the diglyceride fat and oil composition prepared in Examples 1 to 4 was shown in Table 1 below, and Examples 1 to 4 above. The conjugated linoleic acid ester of phytosterol or phytostanol, free conjugated linoleic acid and free phytosterol, which are bound to diglycerides prior to molecular distillation, are measured in Table 2 below.

(Unit: weight%) division Example 1 Example 2 Example 3 Example 4 Monoglycerides One 0.5 0.3 0.1 1,2-diglyceride 28.3 25.4 24.5 23.0 1,3-diglyceride 54.3 58 60.5 63.1 Triglycerides 12.4 12.9 12.7 12.9 Free conjugated linoleic acid 0 0 0 0 Free phytosterol 4 3.2 2 0.9

division Example 1 Example 2 Example 3 Example 4 Conjugated linoleic acid esters of phytosterol or phytostanol 90.9 94.95 97 99.1 Free conjugated linoleic acid 0.1 0.05 0 0 Free phytosterol 9 5 3 0.9

(Comparative Example 1)

1300 g of monoglyceride, 20 g of conjugated linoleic acid, and 5 g of lipase were mixed in a 2 L round flask equipped with a stirrer, and stirred and stirred at a stirring speed of 150 rpm, and then reacted at a stirring speed of 150 rpm at 60 ° C. for 10 hours. A diglyceride fat and oil composition containing was prepared.

Hereinafter, the following experiment was performed to find out the weight increase inhibitory effect and cholesterol lowering effect of the oil or fat composition according to the present invention.

Experimental Example

Experimental Example 1

(Weight increase inhibitory effect)

The composition and safflower oil of Examples 1 to 4 and Comparative Example 1 were fed to each group using 10 Sprague-Dawley rats 6 weeks old. In the feeding method, a 50 mg / kg sample was administered orally once a day for 6 weeks separately from the feed. After ingesting the diet for 6 weeks, the rats of each test group were weighed. After that, the rats were killed through the cervical dislocation and each site was dissected, and then pulverized using a blender while adding 3 times distilled water. The pulverized product was dried at 80 ° C., and fat was extracted by Soxlet method using chloroform-methanol (2: 1) solvent. After the extraction was completed, the solvent portion was obtained, dried, and the amount of dried fat remaining was weighed. The change in body fat was measured and the average is shown in Table 3 below.

Pay period Weight (g) Example 1 Example 2 Example 3 Example 4 Comparative Example 1  Safflower oil 0 days 139.5 ± 3.4 138.4 ± 3.9 139.8 ± 4.6 138.5 ± 3.6 139.4 ± 3.6 141.0 ± 3.3 2 weeks 262.1 ± 7.5 259.3 ± 6.1 265.1 ± 6.3 269.5 ± 6.5 276.9 ± 6.9 294.7 ± 4.1 3 weeks 338.9 ± 10.1 339.2 ± 9.3 339.1 ± 9.5 334.4 ± 10.2 345.6 ± 10.6 359.1 ± 11.4 6 Weeks 359.4 ± 9.5 354.5 ± 9.4 360.2 ± 10.6 364.3 ± 11.1 375.8 ± 11.6 402.0 ± 11.5 Body fat content (g) 35.6 ± 2.3 34.2 ± 2.9 32.8 ± 2.1 30.3 ± 2.6 43.6 ± 3.5 98.1 ± 6.3 Body fat content (%) 8.9 ± 1.1 9.5 ± 1.2 10.1 ± 0.8 8.5 ± 0.7 11.8 ± 1.2 26.5 ± 2.5

As can be seen in Table 3, the maintenance composition-treated group of the present invention showed a tendency to decrease the increase in body weight compared to the administration group fed safflower oil (Safflower oil) and was found to be significantly lower body fat mass. In addition, it was found that the oil-fat composition administration group of the present invention showed a tendency to suppress weight gain and significantly inhibited the increase of body fat than Comparative Example 1, which is a high-purity diglyceride composition containing conjugated linoleic acid.

Experimental Example 2

(Cholesterol lowering effect)

Three-week-old Sprague-Dawley male rats were reared 10 per group. First, in the normal diet, cholesterol and cholic acid were homogenized at concentrations of 1% and 0.5%, respectively, and then mixed and fed for 1 week to raise blood cholesterol levels. While feeding the same feed as described above, the diglyceride fat and oil compositions of Examples 1 to 4 and Comparative Example 1 were respectively administered. The dose of the sample was 0.18 g / kg / day, and after one week, the total blood cholesterol level, HDL (High Density Lipoprotein) cholesterol, and LDL (Low Density Lipoprotein) cholesterol were measured. In order to measure the blood cholesterol level, blood was collected from the tail vein of the rat, left at room temperature for 2 hours, and centrifuged (6000 rpm / 20 min) to separate serum. 300 μl of cholesterzyme (Aigen Chemistry) was added to 20 μl of serum and reacted at 37 ° C. for 10 minutes. The absorbance was measured at 500 nm using an ELISA reader, and the cholesterol concentration was measured using a standard curve.

<Total Cholesterol Level in Blood> sample Before sample administration (mg / dl) After 1 week (mg / dl) ^a % degradation Control 181.90 ± 50.76      136.40 ± 14.50 Example 1 173.10 ± 12.26 103.20 ± 7.59 ^b 24% Example 2 171.48 ± 11.26 99.75 ± 11.41 ^b 27% Example 3 169.28 ± 12.21 101.54 ± 8.51 ^b 26% Example 4 172.65 ± 11.57 102.87 ± 7.96 ^b 25% Comparative Example 1 172.80 ± 11.32 116.21 ± 12.21 ^b 15%

^a rate of decrease in total cholesterol concentration compared to the control group after 1 week

^b p <0.05 (significance with control)

Blood HDL-Cholesterol Concentration sample Before sample administration (mg / dl) After 1 week (mg / dl) Control 23.28 ± 5.77 24.11 ± 8.42 Example 1 22.14 ± 7.65 25.80 ± 4.51 Example 2 23.21 ± 7.61 26.00 ± 6.43 Example 3 23.53 ± 5.46 24.89 ± 4.82 Example 4 22.00 ± 5.83 26.00 ± 6.54 Comparative Example 1 21.50 ± 7.67 25.84 ± 6.59

Blood LDL-Cholesterol Concentration sample Before sample administration (mg / dl)   After 1 week (mg / dl) ^a % degradation Control 192.64 ± 42.13 110.94 ± 24.35 Example 1 153.76 ± 16.97 72.51 ± 21.46 ^b 35% Example 2 151.13 ± 15.43 73.97 ± 15.83 ^b 33% Example 3 152.64 ± 17.97 72.38 ± 14.19 ^b 35% Example 4 151.41 ± 17.79 71.60 ± 26.64 ^b 35% Comparative Example 1 164.65 ± 16.57 78.46 ± 11.19 ^b 29%

^a rate of decrease: the rate of decrease of total LDL-cholesterol concentration compared to the control group after 1 week of sample administration.

^b p <0.05 (significance with control)

As can be seen in Tables 4 to 6, the oil or fat composition of the present invention decreases the cholesterol absorption metabolism in the human body through competition with LDL-cholesterol harmful to the human body, while reducing blood cholesterol concentration, affects the absorption of HDL-cholesterol It could be confirmed that it is not crazy.

As described above, according to the present invention, a diglyceride fat or oil composition comprising a conjugated linoleic acid ester of phytosterol or phytostanol, which has a simple manufacturing method and excellent productivity, and has an effect of reducing body fat and anti-cholesterol, is prepared. Diglyceride fat and oil composition prepared as described above has the effect of lowering the body's cholesterol absorption metabolism through competition with harmful low-density protein (LDL) -cholesterol, and is not digested into body fat when ingested food additives In particular, it will be widely used as a food additive for diet.

Claims (17)

(a) 40 to 99.9 weight percent diglycerides; And (b) residues of monoglycerides, triglycerides or mixtures thereof Including, A high purity diglyceride fat or oil composition comprising conjugated linoleic acid esters of phytosterol or phytostanol at positions 1 and 3 of the diglyceride. The method of claim 1, wherein the conjugated linoleic acid, cis-9, trans-11 CLA; trans-10 cis-12 CLA; cis-7, trans-9 CLA; trans-7, trans-9 CLA; cis-8, trans-10 CLA; trans-8, trans-10 CLA; trans-9, trans-11 CLA; trans-10, trans-12 CLA; cis-11, trans-13 CLA; And trans-11, trans-13 CLA. The method of claim 1, wherein the phytosterol is, High purity diglyceride fat or oil composition, characterized in that the one selected from the group consisting of stigmasterol, spinasterol, camphorsterol, beta-sitosterol, brassicasterol and mixtures thereof. The method of claim 1, wherein the phytostanol is, High purity diglyceride fat or oil composition, characterized in that one selected from the group consisting of stigmastanol, campestanol, cytostolol and mixtures thereof. a) monoglycerides; Conjugated linoleic acid; Phytosterol or phytostanol; And mixing the fats and oils, fatty acids or mixtures thereof and stirring at 10 to 200 rpm; And b) exchanging the stirred mixture of step a) for 1 to 10 hours at 200 to 250 ° C. under a reduced pressure of 0.001 to 0.5torr. Method for producing a high purity diglyceride fat and oil composition comprising a. In claim 5, a) mixing 1 to 80 parts by weight of conjugated linoleic acid, 1 to 80 parts by weight of phytosterol or phytostanol and 1 to 80 parts by weight of fats and oils, fatty acids or mixtures thereof and stirring at 10 to 200 rpm based on 100 parts by weight of monoglycerides ; b) exchanging the stirred mixture of step a) at 200 to 250 ° C. under 0.001 to 0.5 torr for 1 to 10 hours; And c) molecular distillation of the reaction mixture of step b) Method for producing a high purity diglyceride fat and oil composition comprising a. In claim 5, The molar ratio of the monoglycerides and fats and oils, fatty acids or mixtures thereof is 1: 2 to 1: 80, characterized in that the manufacturing method of high purity diglyceride fats and oils composition. The method of claim 5, wherein the phytosterol is, A method for producing a high purity diglyceride fat or oil composition, characterized in that the one selected from the group consisting of stigmasterol, spinasterol, camphorsterol, beta-sitosterol, brassicasterol and mixtures thereof. The method of claim 5, wherein the phytostanol is, A method for producing a high purity diglyceride fat or oil composition, characterized in that it is stigmastanol, campestanol, cytostolol. The method of claim 5, wherein b) the temperature of the exchange reaction, Method for producing a high purity diglyceride fat and oil composition, characterized in that 200 to 230 ℃. The method of claim 5, wherein the holding, A method for producing a high purity diglyceride fat or oil composition, characterized in that selected from the group consisting of soybean oil, rapeseed oil, cottonseed oil, jade oil, olive oil, palm oil, palm kernel oil, palm oil, safflower oil and mixtures thereof. The method of claim 5, wherein the fatty acid, Saturated or unsaturated fatty acids having 2 to 24 carbon atoms, oleic acid, soy fatty acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, linolenic acid, Docosahexaenoic acid (DHA) and mixtures thereof Process for the preparation of high purity diglyceride fats and oils composition, characterized in that selected from. a) mixing monoglycerides, phytosterols or phytostanols, conjugated linoleic acid and lipases and stirring at 10 to 200 rpm; And b) exchanging the stirred mixture of step a) under stirring at a speed of 10 to 200 rpm, a temperature of 30 to 60 ° C, and at a pressure of 0.001 to 0.5 torr for 1 to 10 hours. Method for producing a high purity diglyceride fat and oil composition comprising a. In claim 13, a) mixing 1 to 80 parts by weight of phytosterol or phytostanol, 1 to 80 parts by weight of conjugated linoleic acid and 1 to 50 parts by weight of lipase with respect to 100 parts by weight of monoglyceride and stirring at 10 to 200 rpm; b) exchanging the stirred mixture of step a) under a stirring speed of 10 to 200 rpm, a temperature of 30 to 60 ° C., and a pressure of 0.001 to 0.5 torr for 1 to 10 hours; And (c) molecular distillation of the reaction mixture of step b) Method for producing a high purity diglyceride fat and oil composition comprising a. The lipase of step a), Lipozyme, 1.3-position specific lipase, non-position specific lipase, lysopus with 1,3-position specificity, and geotriose with unsaturated fatty acid specificity, wherein the high purity diglyceride fat and oil composition is selected from the group consisting of Manufacturing method. The method of claim 13, wherein the phytosterol is, A method for producing a high purity diglyceride fat or oil composition, characterized in that the one selected from the group consisting of stigmasterol, spinasterol, camphorsterol, beta-sitosterol, brassicasterol and mixtures thereof. The method of claim 13, wherein the phytostanol is, A method for producing a high purity diglyceride fat or oil composition, characterized in that it is stigmastanol, campestanol, cytostolol.